By Giovanni Sartori
Used within the creation of a large variety of advantageous chemical substances and prescribed drugs, the Friedel-Crafts acylation response represents an artificial strategy of nice curiosity to natural chemists of academia and undefined. approximately forty years because the final significant treatise at the subject and reflecting the becoming emphasis on green technology, Advances in Friedel-Crafts Acylation Reactions: Catalytic and eco-friendly methods makes a speciality of tips on how to make this response extra economically and environmentally pleasant through the use of green acylating stipulations, hence minimizing the formation of waste and lowering construction costs.
Divided into 4 components, the booklet explores stoichiometric acylations, catalytic homogeneous acylations, catalytic heterogeneous acylations, and phenol acylations. it really is dependent in keeping with the function performed via the catalyst within the activation of reagents in addition to within the diversified modes of regioselectivity encountered within the acylation of arenes, fragrant ethers, and phenols.
Incorporating examples of all acid-catalyzed Friedel-Crafts acylation reactions, the textual content considers vintage Lewis and Brönsted acid kinds besides extra cutting edge and complicated multicomponent superacid catalysts. those diversity from infrequent earth triflates or triflimides and their blend with ionic beverages to metal-promoted zeolites and zeotypes, clays, polymetal oxides, sulfated zirconia, heteropoly acids, and Nafion. The booklet emphasizes the most important business purposes, delivering a severe evaluation of the diversities, merits, and downsides of homogeneous and heterogeneous catalysis.
Helping readers to raised comprehend the mechanism of the Friedel-Crafts acylation, the examples within the e-book substantiate the advance of more advantageous catalysts and extra selective techniques completed over the past few many years, permitting to embark on a more secure and extra effective synthesis of fragrant ketones for the manufacture of a big selection of products.
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Utilized in the construction of a large variety of nice chemical substances and prescription drugs, the Friedel-Crafts acylation response represents a man-made technique of nice curiosity to natural chemists of academia and undefined. approximately forty years because the final significant treatise at the subject and reflecting the turning out to be emphasis on eco-friendly expertise, Advances in Friedel-Crafts Acylation Reactions: Catalytic and eco-friendly procedures makes a speciality of the best way to make this response extra economically and environmentally pleasant through the use of eco-friendly acylating stipulations, therefore minimizing the formation of waste and lowering creation charges.
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Extra info for Advances in Friedel-Crafts Acylation Reactions: Catalytic and Green Processes
In general, experimental conditions can be set up in order to efficiently synthesize cyclic aromatic and heteroaromatic ketones. Good yields of cyclic aryl ketones are achieved with arenes, provided they are not very electron deficient. 23 The reaction can also be performed in the presence of protic acid; thus, 3‑(3,5‑dibromophenyl)propanoic acid is directly converted into 2,4‑dibromoindanone by treatment with polyphosphoric acid in 53% yield. The corresponding acyl chloride can be converted into the same product upon treatment with iron trichloride only in 45% yield.
EP Patent 488,638. 18. Marshall, W. , Sigmund, S. , and Whitesitt, C. A. 1988. Process for leuko triene antagonists. S. Patent 4,777,299. 19. Marshall, W. , Sigmund, S. , and Whitesitt, C. A. 1988. Process for inter‑ mediates to leukotriene antagonists. S. Patent 4,777,298. 20. , Desmurs, J. , and Mioskowski, C. 2002. Directed ortho‑metalation, a new insight into organosodium chemistry. Angew. Chem. Int. Ed. 41: 340–343. 30 Advances in Friedel–Crafts acylation reactions 21. , and Murakami, Y. 1997.
The catalyst can be recycled, showing the same activity after four runs. 6). 55 Thus, 1‑butyl‑4‑methylpyridinium bis‑ triflimide ([4‑MBP][NTf2]) represents a suitable ionic liquid as it shows negligible mass loss when extracted with supercritical carbon dioxide and apparently no negative influence on metal triflate catalytic activity. 0 h−1]. 61 Reactions are carried out at high temperature (180°C–250°C) without solvent in a sealed glass tube, affording higher yields in aromatic ketones than classic Lewis acids; however, experimental conditions must be accurately optimized since the high temperature and the very hard Lewis acidity of the catalyst seems to promote undesirable side reactions.